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Manchester United’s season reached a new low as they slumped 2-0 in the Champions League at Olympiakos on Tuesday.

Europe’s elite competition is the Red Devils’ last remaining chance to win a trophy in this campaign but David Moyes’ side face a mountain to climb to reach the quarter-finals in the second leg at Old Trafford after producing arguably their worst performance of the season.

With United already out of the Capital One Cup and the FA Cup and trailing Premier League leaders Chelsea by 15 points with 11 games to play, here are the key games where it’s gone wrong for Moyes in his season.

Baggies defeat sums up Premier League seasonIt’s Saturday, September 28 and United’s worst start to a league campaign since 1989-90 was confirmed as West Brom rack up their first win at Old Trafford since 1978 thanks to Saido Berahino’s winner. Just for the record, other teams breaking their hoodoo against United this season have been Stoke (earning their first win since 1984), Newcastle (first win at Old Trafford since 1972) and Everton (first win at Old Trafford since 1992).

Fabio is sent off by referee Mike Dean against Swansea (Picture: Reuters)

Swans extend United’s FA Cup waitUnited haven’t won the FA Cup since 2004, and the wait was extended after Swansea claimed a shock 2-1 third-round win at Old Trafford on January 5. The hosts were rocked when Fabio was red-carded ten minutes from time for bringing down Jose Canas and Wilfried Bony’s 90th-minute winner gave the Welsh side a win at the Theatre of Dreams for the first time in their history.

Capital One Cup penalties horrorUnited’s season plunged to new depths as Sunderland won on penalties at Old Trafford to secure a Capital One Cup final place against Manchester City. Sunderland were 2-1 up from the first leg but with four United players missing from the spot in the shoot-out Moyes was left to explain another poor performance from his side, admitting: ‘It was disappointing but we didn’t play well.’

Darren Fletcher and Steven Fletcher do battle in the Capital One Cup (Picture: Getty)

August 31, 2013
Not a date of any competitive match, but do United’s problems date back to the close of the summer transfer window? Marouane Fellaini from Everton was Moyes’ sole addition to a title-winning squad he inherited from Sir Alex Ferguson, which was always going to need some beefing up. Leighton Baines, Athletic Bilbao midfielder Ander Herrera, Real Madrid full-back Fabio Coentrao, Barcelona’s Cesc Fabregas and Bayern Munich midfielder Thiago Alcantara were all touted as big-name arrivals but none were secured.